How to Craft a Career Path: Easy Step By Step

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Too many times, we find ourselves working hard to drive someone else’s career goals forward.

There, we said it (and boy, that bluntness doesn’t feel good to acknowledge.)

It’s true, though. Sad…unfortunate even, but completely true.

We feel lost in the shuffle, our goals and aspirations pushed to the side in order to serve someone else’s. We wander around, looking for direction… OUR true North, only to get frustrated and disengaged and, well, we just keep plugging along day after day like that.

This mainly happens due to our human tendency to ‘follow the leader’. We all too happily correlate THEIR success to our own, because we get praise when they reach goals through our actions. Traditionally, though, this is a recipe for your own eventual disenchantment with your job, your leadership and potentially the organization that you once saw so much value in joining!

This companion article, to our latest episode on Crafting a Career Path for Beginners (watch short lesson HERE or listen to the longer, discussion-based podcast HERE), will go deep into the groundwork that ALL employees, who have their own goals and dreams for their employment within an organization, should be doing.

In order to be truly satisfied, we all need to be working towards something that will reward us and propel us in the direction we want to go in. We can’t be fully satisfied watching others succeed from our efforts with no reward or feeling of accomplishment of our own. Seeing this pattern over and over as people get promoted and we stay in the same place is exhausting… and very discouraging.

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Our goal with this article (and the accompanying video and podcast) is to readjust that perspective BACK onto yourself. Changing HOW you look at your job and your success starts with feeling like you are working towards something that you want. And after years of people in higher positions telling us what that is, it is hard to know where to begin, what is actually realistic for you and how to take that first step (and keep going)!

Today, we’re going to put in the work and prepare you to start (or start fresh) with a path that is YOURS.

We will cover what you need to know in order to craft a well-thought-out career path for yourself and introduce the 5 actions you must be comfortable doing in order to get the information you need to do so!

Let’s dig in.


So, what do we mean by ‘crafting your path’? There are 5 key elements you must understand before you can formally create one. They are:

  • Knowing your starting point (aka your current position and skill set)
  • Knowing what you’re passionate about
  • Knowing the lateral & vertical position movements that you can make with your current skill set to tap into that passion
  • Knowing what you need to learn to reach beyond your current position and move along the path to your end goal
  • Knowing WHO can help guide you along your path

In order to understand the points listed above, you need to become very comfortable doing the following 5 things:

  1. Asking Questions
  2. Learning how your current skills transfer to other functions
  3. Knowing where to go to learn new skills needed for advancement or moving into your desired specialty/function
  4. Building meaningful work relationships that bring advocates to your side as guides and mentors
  5. Knowing how to create goals that serve and directly relate to the path you desire to take

To help you get started, we’ve put together actions that you can take, STARTING TODAY, to begin crafting your career path. Below, you will find an outline and guidance on each of the above 5 skills needed to comfortably build that path: understanding where you’re starting from, where you can go, how to get started and ultimately, how to keep yourself ON that path.


Now, let’s just review what you will need to know in order to create your career path. The basic formula is:

  • Knowing your starting point and your skill set – Skill assessment is a MUST to be able to accurately understand your potential trajectory with an employer. Starting HERE is the best way for you to level-set and begin crafting that career path.
  • Knowing what you are passionate about (aka: what you TRULY love to do, which most likely will guide you where you want to go) – It’s the logical next step to creating your path. When you know what you love, you can ask ‘how do I get there, from here?’ much more comfortably. It is easier for you to approach people in roles you find compelling and ask them how they got to where they are, and what the steps they took to achieve that role. Without knowing what you love and want out of your employment, you cannot see how your current skills apply… or what additional skills might be needed. Knowing ‘your passion’ is a crucial step, as it aids you in not accidentally starting down the wrong path, which is leading you away from your goals and passions rather than towards them.
  • Knowing your lateral/vertical options – understanding what’s on either side, up or down from your starting point, is another important part of creating a career path that ultimately takes you where you want to go. If your aspiration is to switch lanes or functions, this step is even more important, as you may be considering stepping laterally, or even slightly down in order to position yourself in the right lane to achieve the career goals you have set for yourself. Asking the right questions and leveraging meaningful relationships to help answer these questions is the primary way you can align yourself correctly and fully understand the steps needed to move along the path you create.
  • Knowing what you need to learn – This is simply being honest about your skill gaps (from your assessment). It is understanding where you need to go to learn and committing to the work you must put in to gain these skills in order to move along the path you’re creating for yourself. Asking questions of the right people, understanding your organization’s education and learning systems and committing to this self-development is a non-negotiable for anyone who wants to progress in their career. This step is not anyone else’s responsibility but your own, though you may have created advocates for your advancement and growth by making meaningful relationships and finding mentors along your path.
  • Knowing who can help – Finding guides to help you along your career path is the final (not first) step in creating one, and the reason is this: it is no one else’s responsibility to help you succeed in your personal career goals. Harsh? Not really. In reality, if someone else is driving your career growth, you might be serving someone else’s success more than your own… which likely means, you need to put more effort into making sure the path you are on is TRULY YOURS. All bosses want their employees to be successful, but the most successful employees… those that navigate the ladder and rise through the ranks quickest, are always those who have a clear understanding of WHAT THEY WANT (and who can help them get there). Whether having a mentor, coach or teacher is best for you, there is no denying that we learn better with guidance, experience less stumbles, deeper learning and lasting skills.

Now, in order to know what’s above, here’s a quick reference chart to help you visualize the HOW you gain that knowledge.

Now let’s dig into these actions. (Note: #1 and #2 are lengthy because MASTERING THOSE skills makes everything else easier!)

#1. Asking questions:

Being able to ask questions about one’s career might sound simple enough, but in our experience as senior level leaders, it doesn’t happen nearly as often as you would expect.

And, when questions are asked, they’re often vague, not fully thought out or are simply probing for a ‘quick fix’ by getting their boss’s direction. “What do you think I should do, boss?” can easily turn into a career path that has a feeling of ‘well, my boss told me I needed to do this so here I am’ attached to it, and it is less likely to be tackled with enthusiasm as it’s not YOUR GOAL, but rather you boss’s direction.

Here are a few examples of great questions that you can ask of your boss to help you get clarity around your career goals and creating an actionable path for yourself:

  1. In my current role, what would the steps be for me to get to “X”?

2. I am most passionate about “X” part of my role, what other elevated positions tap into that passion?

3. I am really interested in moving into “X” specialty for our organization… are there lateral moves I could take to get me into the right lane for that?

4. I see my strongest skills as “X, Y, & Z”… what skills to you think I’m strongest in?

5. I see that to get to my goal of “X” I need to get stronger in “Y & Z” skills, do you have any suggestions on where or how I could strengthen them?

If you are seeing a pattern in the above suggested questions, you’re not mistaken. Each one of these questions is controlled by YOU, the employee, bringing your thoughts into the discussion FIRST, and then asking for your boss’s input. NOT vice versa.

Asking questions in this manner not only places you more in control of the discussion (keeping the focus on your goals) but it also targets your supervisor’s responses to be the most impactful for you in a short amount time.

These questions require you to know some important pieces of information BEFORE you ask them, too, like your passion, your skill set, your intentions, your shortcomings. Showcasing this information to your boss has an immediate (and positive) byproduct – they know you’re serious and have done the leg work. Seeing this level of commitment almost always creates a boss who will invest more time in your development and path.

Remember: vague questions get vague answers, which generally help no one and waste time. Alternatively, and possibly worse, vague questions open the door for misunderstanding, which often leads to frustration on both sides.

Put the work in ahead of time and ask the RIGHT questions. You won’t regret it!

#2. Skill Assessment/Transferrable Skills

It’s critical for anyone looking to move up aggressively within an organization to be able to assess their skill set. It is even more important when someone is looking to shift into a different function to achieve their career goals.

Understanding your current skills and how they are transferrable, as well as potential skill gaps is something every employee with career goals should be doing. We suggest doing this quarterly, so you can see your learnings and keep an accurate assessment at the ready, if your goals change or outside forces impact your employment situation.

If you are doing this for yourself, simply listing your strengths, weaknesses and your ‘can do but avoid’ skills is a great start.

As a leader, one of the best ways to help guide employees through this process is to have them make that list and then ask them what other functions of the team those skills might be useful for. This method of starting where the employee IS, versus looking at the job description of where they want to go, is important because it forces the employee to be honest about what they are capable to doing RIGHT NOW. 

Assessing skill is not about assessing POTENTIAL but about understanding where you are now and what you can do. It has everything to do with teaching the value of self-awareness and the steps required in order to work towards (and achieve) a goal. 

  • Once you list your skills, you can easily pull out that same desired job’s description and discuss how that list of current skills fits into it. If there are gaps, you can create a development plan… but the most important thing is to make sure you are looking at your career path from the right vantage point. 
  • New skills needed can easily be identified if you use this method of assessing skills: listing your current position/work skills then seeing how they stack up to the desired advancement’s skill requirements. 
  • Seeing the gaps in skill gives you a very simple list of learnings and development needed to help you along your path.

#3. Where do I go to learn?

Yes, it’s true that every major organization has a Learning & Development program or a centralized hub of lessons and skill building materials that are available.

What’s NOT always true, is that it is easy to find, easy to navigate or even easy to access for to someone looking to drive their own development. 

Even though they might not be obvious, you need to know what resources you have for learning! Without them you will struggle to work on your own development.

Here are a few things to consider when looking for those resources:

  • To be successful in your career path within a specific organization, you need to optimize your skills within its proprietary tools. They are designed to fine tune you to the organization’s business model, strategies and mission. In other words, walking the walk and talking the talk within their specific corporate culture and framework.
  • That’s not to say that you can’t supplement your learnings in core skills elsewhere, but not taking advantage of what is available would do you a disservice. Seek your organization’s tools FIRST, supplement with additional resources where you find gaps.
  • Speaking with your supervisor to find the location of these resources is the first step, next would be the administrative team for your location (as they generally are in charge of managing and rolling out trainings), and the last step would be HR. 

#4. Building Meaningful Relationships

This isn’t about networking. 

Creating advocates for your development and true mentor relationships requires work. It requires you to understand how someone can help you, and what you bring to the table for them within that relationship in order to create something that benefits both parties. 

Examples and reminders:

  • Want to be a merchandiser, but are currently in sales? Who is the best merchandiser and how can you help THEM so in turn they teach, guide and mentor YOU along the way? 
  • Meaningful relationships are not transactional or short lived, but longstanding mentorships that stay with you, even after you no longer work with, or for that other person, anymore. Meaningful relationships always involve mutual benefit. 
  • Cultivated, those types of relationships gain you advocates for your career advancement that are genuinely invested in your growth. A networked recommendation is just a piece of paper and can end up in the ‘shred-it’ pile all too quickly. 

#5 Creating Goals that serve the Path

Lastly, creating and understanding your path is meaningless without that first STEP. Once you’ve done the legwork of understanding WHERE you want to go from WHERE you are starting, creating actionable and realistic goals for yourself that move you along that path must happen.

We have a whole episode around creating goals (video HERE and podcast HERE,) as well as a detailed companion article that goes into it HERE, to teach you some easy steps for creating actionable and realistic goals.

And finally, remember that YOUR ADVANCEMENT is not really anyone else’s responsibility but your own. If you want it, go after it! There are many who can help you along the way, but YOU get yourself promoted… it’s not your boss’s job to get you promoted. Finding the opportunities to ASK those questions, LEARN new skills and CREATE advocates to guide and mentor you should be something YOU take on.

Whether you are an individual looking to craft a path for yourself, or a leader looking to master the skill of helping your employees navigate the process, we hope this article gave you clarity around the process, the requirements and the actions in order to do so.

See you soon!

Remember, our weekly articles to help you focus on your own development can be found here on our BLOG or through LinkedIn.

Follow us on either platform to stay up to date with the latest content!

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